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Radioiodination method

Active Publication Date: 2013-11-28
GE HEALTHCARE LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a method for radioiodination of biological targeting molecules (BTMs) that is applicable to a range of BTMs and can be carried out under mild conditions. The method uses non-reactive precursors and functionalised BTMs to introduce radioiodine at the latest possible stage, minimizing non-specific radioiodination and ensuring high purity of the non-radioactive chemicals. The radioiodination is achieved through a single, straightforward and high-yielding step. The resulting products have been found to be stable with respect to metabolic deiodination, making them suitable for in vivo imaging. The method is also adaptable to automated synthesizer apparatus. This invention provides a valuable tool for the field of biological molecule imaging.

Problems solved by technology

Eersels et al concluded, however, that there was no overall preferred radioiodination method, since the choice depends on the nature of the compound to be radioiodinated.
WO 2006 / 116629 does not, however, provide any specific teaching on how to apply the method to the radioiodination of biological molecules.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of 1-Phenyl-4-(tributylstannyl)-1H[1,2,3]triazole (Prophetic example)

[0126]

[0127]Phenylazide can be obtained from Pfaltz & Bauer, Inc., or can be synthesized by the method described in J. Biochem., 179, 397-405 (1979). A solution of tributylethynyl stannane (Sigma Aldrich; 400 mg, 1.27 mmol) in THF (4 ml) is treated with phenylazide (169 mg, 1.27 mmol), copper (I) iodide (90 mg, 0.47 mmol), and triethylamine (256 mg, 2.54 mmol) at room temperature over 48 h. The reaction is then filtered through celite to remove copper (I) iodide and chromatographed on silica in a gradient of 5-20% ethyl acetate in petrol. The second fraction is collected and concentrated in vacuo to give the 1-phenyl-4-(tributylstannyl)-1H[1,2,3]triazole as a colourless oil.

example 2

Preparation of [123I]-1-phenyl-4-iodo-1H[1,2,3]triazole Using Peracetic Acid as the Oxidant (Prophetic example)

[0128]

[0129]To sodium [123I] iodide, received in 5-20 μL 0.05M sodium hydroxide is added ammonium acetate buffer (100 μL pH 4.0, 0.2M), sodium [127I] iodide (10 μL 15 mg / 10 ml 0.01M sodium hydroxide, 1×10−8 moles), peracetic acid (PAA) solution (10 μL 0.01M solution, 1×10−8 moles) and finally, 1 phenyl-4-tributylstannyl-1H[1,2,3]triazole (Example 1; 23 μg, 1×10−7 moles). The reaction mixture is incubated at room temperature for 15 minutes prior to purification by HPLC.

example 3

Preparation of [123I]-1-Phenyl-4-iodo-1H[1,2,3]triazole Using an Iodogen Tube as the Oxidant (Prophetic example)

[0130]

[0131]To an iodogen tube (Thermo Scientific Pierce Protein Research Products), pre-wet with 1 ml pH 7.4, 25 mM sodium phosphate buffer and subsequently decanted is added sodium phosphate buffer (100 pH7.4, 25 mM), and sodium [123I] iodide received in 5-20 μL 0.05M sodium hydroxide. The reaction is allowed to stand at room temperature for 6 minutes with agitation prior to the addition of 1 phenyl-4-tributylstannyl-1H[1,2,3]triazole (Example 1; 23 μg, 1×10−7 moles). The reaction mixture is incubated at room temperature for 15 minutes prior to purification by HPLC.

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Abstract

The present invention provides a novel method of labelling biological targeting molecules (BTMs) of interest with radioiodine. Also provided are functionalised BTMs useful in the method, as well as methods of preparing such functionalised BTMs under mild conditions.

Description

FIELD OF THE INVENTION[0001]The present invention provides a novel method of labelling biological targeting molecules (BTMs) of interest with radioiodine. Also provided are functionalised BTMs useful in the method, as well as methods of preparing such functionalised BTMs under mild conditions.BACKGROUND TO THE INVENTION[0002]Methods of incorporating radiohalogens into organic molecules are known [Bolton, J. Lab. Comp. Radiopharm., 45, 485-528 (2002)]. For the case of 123I-labelled radiopharmaceuticals, Eersels et at [J. Lab. Comp. Radiopharm., 48, 241-257 (2005)] have compared the 4 principal synthetic routes:[0003](i) oxidative radioiodination;[0004](ii) nucleophilic isotopic exchange;[0005](iii) nucleophilic non-isotopic exchange;[0006](iv) electrophilic labelling.[0007]Route (iv) typically involves the use of an organometallic precursors, such as trialkyltin, trialkylsilyl or organomercury or organothallium derivative. Of these, the radioiododestannylation route was acknowledged ...

Claims

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Application Information

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IPC IPC(8): C07B59/00A61K51/08
CPCC07B59/008A61K51/08A61K51/0453C07B59/002C07D249/06C07D261/08
Inventor AVORY, MICHELLEWADSWORTH, HARRY JOHNNAIRNE, ROBERT JAMES DOMETT
Owner GE HEALTHCARE LTD
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